9 Terrific Hometown Tours

Historic Milwaukee Inc. Volunteers lead walking tours (and one boat trip), including a daily architecture tour that's a fun way to get fresh air during the work day. From $10. (414) 277-7795; historicmilwaukee.org

Why The architecture is interesting, but I'll remember the people and stories behind the buildings: territory disputes, the first white child (named Milwaukee) and the Polish immigrants who populated Brady Street in the 1800s. -- Manya Kaczkowski

Historic Gateway Neighborhood Corp. Actors dressed as historical figures chat with visitors during free tours downtown through a summertime program called Take a Hike! On weekends, dogs are welcome. (216) 771-1994; historicgateway.org

Why Lighthouse steps (but no lighthouse) and the buried storefront of a 19th-century theater? Throw in a "chance" encounter with John D. Rockefeller, and I'm suddenly hooked on the city's history. -- Sarah Routh

Why You'll hear the stories of locals you've never heard of (and a few you have). Near gangster John Dillinger's grave, you'll see the resting place of a World War I soldier who died in the 1918 influenza epidemic. And he's the one who captured my imagination. -- Danny Lee

Columbus Food Adventures Five food-theme van and walking tours include a dessert sampler, a German Village walking tour and a taste of the city's best taco trucks. From $45. (614) 440-3177; columbusfoodadventures.com

Why Ditch your fears of "roach coaches" or language barriers, and learn how to order the amazing red enchiladas from Los Potosinos. -- Cynthia Earhart

Durham Museum Chatty, knowledgeable guides hop aboard Omaha's Ollie the Trolley (a local sightseeing staple) for five history tours that start at stunning Union Station (pictured at left). From $15 (402) 444-5071; durhammuseum.org

Why Seeing the stained-glass windows, variegated marble and stately porte cocheres of the city's grand mansions made me daydream about the glamorous events that once led stars and presidents to these doors. -- Tina King

Chicago Architecture Foundation Architectural river cruises (several companies offer them) are a must-do, but if you want to delve deeper, the CAF's diverse tour menu includes Skyscraper Express, Macy's on State Street and Downtown Deco. From $5 (312) 922-3432; architecture.org

Why Chicago is an architectural think tank, and every CAF tour reveals something I didn't know about: a Henry Moore sculpture casually tucked in a lobby or Louis Sullivan stained-glass windows casting colored light on the place where Chicago Gospel was born. -- Kit Bernardi

Why F. Scott Fitzgerald grew up around here. Seeing how his neighbors used their massive homes to show off their wealth and power, I understood in a new way his fascination with (and resentment of) affluence. -- Gustave Axelson

Queen City Underground Evening tours of historic Over-the-Rhine take curiosity seekers through the crypt of St. Francis Church and down a makeshift stairwell to a Gothic cellar that once kept barrels of German beer cool. From $20. (859) 951-8560; queencityunderground.com

Why Great storytelling backed up by extensive research (and the fact that you have to sign a safety waiver) makes it feel like you'll literally step into the colorful world of corrupt politicians, boxing stars, Franciscan monks, strong men and the first commissioner of baseball. -- C.M. Tomlin